Young and Profiting with Hala Taha - Kevin O'Leary: The Game-Changing Habits That Set Top Entrepreneurs Apart | Entrepreneurship | YAPLive | E376

Episode Date: December 1, 2025

Now on Spotify video! Starting a business is brutally hard, and Kevin O’Leary is a living example of that truth. Despite early failures, he went on to build and sell The Learning Company for $4.2 b...illion in one of the most competitive tech markets in history. As an investor in over 50 companies, he can spot true entrepreneurs from a mile away and knows exactly what it takes to stay in the game. In this episode, Kevin exposes the harsh realities of entrepreneurship and shares the essential traits, skills, and strategies that separate successful founders from those who fail. In this episode, Hala and Kevin will discuss: (00:00) His Early Life and Path to Entrepreneurship (06:04) Kevin’s Rules for Scaling Beyond $5M (14:05) Lessons From a $4.2B Business Exit (22:37) Transitioning From Operator to Investor (27:42) Managing the Highs and Lows in Business (32:32) What Makes a Successful Entrepreneur? (36:51) Rating the Traits of True Entrepreneurs (46:29) High-Performance Habits for Entrepreneurs (01:01:16) The Power of Creator Entrepreneurship Kevin O’Leary is a serial entrepreneur, venture capitalist, and television personality, best known as “Mr. Wonderful” on ABC’s Shark Tank. He co-founded and built The Learning Company, which was later sold for $4.2 billion, making it one of the largest tech exits of its time. Kevin is also the Chairman of O’Leary Ventures, as well as a bestselling author, global speaker, and advocate for entrepreneurship and financial literacy. Sponsored By: Indeed - Get a $75 sponsored job credit to boost your job's visibility at Indeed.com/PROFITING  Shopify - Start your $1/month trial at Shopify.com/profiting.  Revolve - Head to REVOLVE.com/PROFITING and take 15% off your first order with code PROFITING  DeleteMe - Remove your personal data online. Get 20% off DeleteMe consumer plans at to joindeleteme.com/profiting  Spectrum Business - Visit Spectrum.com/FreeForLife to learn how you can get Business Internet Free Forever. Airbnb - Find yourself a cohost at airbnb.com/host  Northwest Registered Agent - Build your brand and get your complete business identity in just 10 clicks and 10 minutes at northwestregisteredagent.com/paidyap Framer - Publish beautiful and production-ready websites. Go to Framer.com/design and use code PROFITING Intuit QuickBooks - Bring your money and your books together in one platform at QuickBooks.com/money  Resources Mentioned: Kevin's Website: kevinoleary.com   Kevin's LinkedIn: linkedin.com/in/kevinolearyshark   Kevin's Instagram: instagram.com/kevinolearytv/?hl=en    Kevin's YouTube: youtube.com/channel  Active Deals - youngandprofiting.com/deals  Key YAP Links Reviews - ratethispodcast.com/yap YouTube - youtube.com/c/YoungandProfiting Newsletter - youngandprofiting.co/newsletter  LinkedIn - linkedin.com/in/htaha/ Instagram - instagram.com/yapwithhala/ Social + Podcast Services: yapmedia.com Transcripts - youngandprofiting.com/episodes-new  Entrepreneurship, Entrepreneurship Podcast, Business, Business Podcast, Self Improvement, Self-Improvement, Personal Development, Starting a Business, Strategy, Investing, Sales, Selling, Psychology, Productivity, Entrepreneurs, AI, Artificial Intelligence, Technology, Marketing, Negotiation, Money, Finance, Side Hustle, Startup, Mental Health, Career, Leadership, Mindset, Health, Growth Mindset, Side Hustle, Startup, Passive Income, Online Business, Solopreneur, Networking

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Starting point is 00:00:00 There's so many people that want to, oh, the market changed. Oh, the competitors changed their prices. Oh, there was dumping on the market from China. Yada, yada, yada, yada, yada, yada, yada, yada, yada. Bullshit, all bullshit. The founder and the CEO, they are the person who failed. Unless I hear that, I never invest in them. In this episode, we're diving deep with the one and only Mr. Wonderful himself,
Starting point is 00:00:23 Kevin O'Leary. Kevin is a world-famous entrepreneur, investor, Shark King star, and a self-made multimillionaire who's turned setbacks, and to strategies for massive success. Entrepreneurship is a disease, actually. It's a virus, and it never set you free. And so you have to know that, and the more successful you are, the harder you work. You're never going to be free.
Starting point is 00:00:41 And then you have to decide, what's my life balanced like? Well, there isn't any. It's a bullshit concept. You know, when I go to a value, a company, there's only two people I want to talk to before the CEO. Just those two people will tell you, is this a good business or not? I want to meet the person running, and I want to meet the head of it. A lot of entrepreneurs forget to do this.
Starting point is 00:01:01 Get that first $5 million really secure in your name. I like that goal. It's a good goal. It's enough to push you, but you're not going to stop working. You're going to keep going. So what needs to change at $5 million to then hit $10 and $30 and $100? At the $5 million point, you need to transition from being the entrepreneur to the leader. And many fail at that point because...
Starting point is 00:01:24 Hello, young and profiters. What does it take to build an empire? sell it for billions and stay on top when the stakes are sky high. In this episode, we're diving deep with the one and only Mr. Wonderful himself, Kevin O'Leary. Kevin is a world-famous entrepreneur, investor, Shark Tank Star, and a self-made millionaire who turned setbacks into strategies for massive success. We'll talk about how Kevin built and sold the learning company for $4.2 billion, why culture clashes, can destroy great businesses, and the biggest lessons he's learned from decades of investing in over 50 companies. Kevin also shares his
Starting point is 00:01:58 secrets to staying focused on what matters, cutting through the noise, managing the emotional roller coaster of entrepreneurship, and using storytelling and personal branding to dominate in today's creator economy. Believe me, you don't want to miss this conversation. And without further delay, Kevin, welcome to Young and Profiting Podcast. Thank you, Hala. Great to be here. I'm so excited for this interview. I've been watching Shark Tank for years. It was actually like the show that me and my family always watched. I think Shark Tank's older than you are.
Starting point is 00:02:27 I wish. But I watched it all the time, and now I'm running a company that's about to hit eight figures this year, and I feel like Shark Tank was really one of the things that inspired me when I was growing up. So thank you for all the work that you've done for young entrepreneurs. Yeah, we're very proud of the platform. We certainly didn't know when we started out what would happen. The first three years, it was canceled three years in a row, and it was kind of interesting.
Starting point is 00:02:53 that Disney just kept it going, and we found out that Will Obey, Iger's wife, was part of the reason. Her kids were watching it. She loved the show. She was an advocate for us, and then, of course, season four, it exploded. It's just like a classic in terms of TV, and you guys have done so much. So, Kevin, you're one of the most recognizable businessmen in the world. You're an extremely successful entrepreneur. But what was Kevin like growing up? You know, I was like any other kid. I was really very interested in that. time in photography, and I was part of the photo club in my high school, and I told my father I wanted to pursue photography and film production, and he said, you're going to starve to death.
Starting point is 00:03:33 You're just not good enough. You've got to realize you're competing with a million other people want to do the same thing, and there's nothing special about what you do. You would think that would be very hard love to hear from his stepfather, but he was factually correct, and it forced me to take a different path to pursue some business education. which ended up being immensely valuable, but not for the education. I learned later. I don't remember anything I did in my MBA at all,
Starting point is 00:04:02 but I met all these people that went on to become leaders in pretty well all 11 sectors of the economy, and I can phone them today and get instantly through to them and use them as my network. Business school is not about, you know, balance sheet training or incomes.
Starting point is 00:04:19 If you're successful, an entrepreneur, you're going to hire a bean counter. So I don't do the book. anymore, but I certainly needed that network to get ahead in those critical years, and I'm glad I did it. I'm glad I spent the time. So an education isn't worthless, although there's lots of billionaires that never finished high school.
Starting point is 00:04:36 Yeah. So if somebody was considering going to college or getting an MBA now, would you say it's necessary or don't do it? No, I wouldn't say it's necessary. I would say it's a, the reason you would do it is to understand for 24 months, you're in a cohort of some of the most incredible people from around the world, because these institutions, I teach at them, these Ivy League schools, they curate an international group of people that are extraordinary.
Starting point is 00:05:04 And it doesn't mean they're all going to be successful, but they all have unique attributes, and they kind of build these cohorts around each other. So there you are put into this place where there's some really smart people challenging your ideas for two years. Yeah. And you have to defend for yourself, but it has nothing to do. You know, it's, when I teach these classes myself, I walk in there and I say, look, everybody,
Starting point is 00:05:31 you're all going to forget me. It doesn't matter. But the real value in this class is you. Is these relationships you're forming in here. You should never forget that. And I think that's a wonderful thing. And if you can get in, it's worth it. And, you know, that to me was what made it worth it.
Starting point is 00:05:52 And now I know that was certainty because I'm decades past it. I got a 4.0 in my MBA, and I don't remember anything from what I actually learned. But I didn't go to an Ivy League school, and I have to say, like, I didn't really get connections from it. So I feel like if you go to an Ivy League school and you can get into an Ivy League school, maybe it's worth it, but otherwise. Well, the brand helps. Harvard helps, MIT helps, any of these Ivy League names, I get it. But I think the education, I'm glad I did it, and it certainly set me up to do. By the way, I went right back into photography afterwards.
Starting point is 00:06:24 But I figured out how to turn it into a business. I started making films for the NHL for Saturday hockey games that built a business. We eventually sold it called Special Plant Television. It was my first exit. So I kind of got in the groove of being an entrepreneur from the things I was passionate about. And that's the secret to entrepreneurship.
Starting point is 00:06:43 You want to do it in something that you're willing to work, 25 hours a day, eight days a week, because some guy in Mumbai or Shanghai is kicking your ass. because they're working that hard. Let's talk about how you actually got your start into entrepreneurship. I heard that you've only had one job in your life and you got fired on the first day. It's true. It's the ice cream story, Magoo's Ice Cream Parlor.
Starting point is 00:07:06 It was the name of it. And I wouldn't scrape the gum off the floor because the girl I was hot for in high school was selling shoes across the mall. She was watching me. I thought the only reason I took the job is to hit on her afterwards. So we got off, you know, 6 o'clock. But, yeah, she whacked me. And it was very humiliating. And actually, it was so important
Starting point is 00:07:27 because it really gave me the understanding of there's the people that own the store and there's the people that scrape the shit off the floor. And I didn't want to be the guy scraping. I wanted to own the store. And I owe her a great, you know, some of gratitude. I went back to find her decades later when I could afford to bulldoze the home mall myself
Starting point is 00:07:48 if I wanted to, They've already been bulldozed. So I never found her. But most entrepreneurs I talk to have that definitive moment that push them on the path towards entrepreneurship. That somehow their lives are changed and they get this burning desire to pursue something where they're in control of their destiny. It doesn't mean they're always successful. But if you don't have that fire, you don't have that passion and you're not willing to take that risk, you're not going to succeed. Yeah.
Starting point is 00:08:13 So you have so much money, right? But you're still working. And you could retire today, of course. So what actually drives you in entrepreneurship? I don't need more money. I need more time. There's so many things I'm pursuing now that interest me. I'm able to invest in almost all of them.
Starting point is 00:08:30 They don't always work out, but enough are successful. I mean, the whole thing about money that a lot of people don't understand, you're going to find this out as time passes, and only the experience of going through it gives you the knowledge, because nobody believes this when, you know, if you're an entrepreneur and you can sell $100,000 of the product to people that are not your relatives, that's the first thing, because your aunt will always buy your shit from you.
Starting point is 00:08:59 Yeah. But that's useless. You've got to sell it to an arm's length person who wants the product and the service independent of the fact that they want to help you. They want to be served a product that helps reduce a pain point for them. They're willing to pay you money for it. If you can do 100,000 of that, you can do 500,000.
Starting point is 00:09:16 If you can do 500,000, you can do 5 million. If you do 5 million, you can do 50. If you do 50 million, you can do half a billion. That's how it goes. But at the 5 million point, that's when the whole system tests you. Because you need to be able to build a team. You need to transition from being the entrepreneur to the leader. Yeah.
Starting point is 00:09:39 And many fail at that point. And I see this when I invest in them. and I have to take them behind the barn and whack them eventually. They're still shareholders, but they don't have the leadership skills, the ability to lead people so that you can get the leverage to build a business past $5 million. But really what's driving you, if you're going to do that, is you're competitive and you want to win. And I never thought about ever the money when we were doing the journey on my big exit,
Starting point is 00:10:11 the learning company, neither of the other nine guys that were, sort of founders. Yeah. We just one day woke up and someone bought our company for $4.2 billion and we were all, you know, filthy rich.
Starting point is 00:10:22 And that didn't change anything. We still went back to work the next day. It's weird, but it just doesn't matter. It's great to have the liquidity, but it doesn't really change your life that much. And so people should understand that. All you really need in the bank to be secure for the rest of your life
Starting point is 00:10:43 is $5 million. dollars. And I tell every entrepreneur that go well past that, the discipline is get five million and put it in T-bills and just look at it. It's just sitting there and don't touch it. Because if Pupu hits the fan, you're still good. What are T-bills in case people don't know? Treasury bills. You know, you can also buy gold but doesn't have any yield. I have T-bills. I roll a bunch of T-bills. That's my F-U account. And it always has been.
Starting point is 00:11:15 I've never touched it. And, you know, I buy dinner with the interest. So you never touch it, and then whatever you make off of it, that's what you spend. Well, that's the protection. I had that goal decades ago. I mean, it's more than five. It's grown over the years. I just leave it in there.
Starting point is 00:11:31 But it's something that gets you, that sets you free. It's a lot of money, but a lot of entrepreneurs forget to do this on their way. Yeah. They keep rolling all the dice all the time. They don't take anything out. And something goes wrong, and they end up with nothing because to its leverage on their business or something, you know, happen.
Starting point is 00:11:56 It's get that first five million really secure in your name and then look at it on your phone every day and say, I've achieved that. Yeah. I like that goal. It's a good goal. It's enough to push you, but it's not enough to make,
Starting point is 00:12:13 make it safe for you and your family. But it's certainly, you're not going to stop working. You're going to keep going. Something that you said reminded me of what Brandon Dawson talked to me about. So he's a co-founder of Cardone Ventures, and he's like a very successful entrepreneur. And he was telling me there's like three pivotal moments for entrepreneurs, like hitting one million, hitting 10 million, and 30 million. And like each one of those stages requires different things. You say, you were just saying like five million to you. is like a pivotal point. So what needs to change at $5 million
Starting point is 00:12:47 to then hit $10 and $30 and $100? Yeah, you won't get past five if you haven't started to build a team because, you know, no one is perfect in all aspects of business. You have to hire to fulfill or fill in. It's like a crack in the wall you put plaster on. You have to find and understand your own weaknesses and hire people that are strong in that attribute
Starting point is 00:13:08 and give them equity in your business, make them your partner. It's sort of like Steve Jobs and Wozniak. I worked for those guys in the early 90s. They were both brilliant, but they had completely different skill sets. They couldn't have made it without each other. It was impossible.
Starting point is 00:13:25 But it's because they had that partnership and they were able to build it together knowing they couldn't do it without each other, you will find out what you're weak at by the time you hit five. You may start it on your own and be just the sole purpose. proprietor, own all the shares, but your cracks will start to show at $5 million.
Starting point is 00:13:45 Now, it might be in logistics, it might be in compliance, it might be in accounting, whatever it is, you have to hire the person that's going to take that off your back so you can focus on your strengths. I'm sales and marketing. That, in that I trust, very few people are better than I am at that. That's arrogant, but I know I'm right. And so that's my competitive weapon. You can't touch me. But I am sure. at logistics. I don't care about worrying about the bookkeeping. I want someone else that knows what they're doing to do that. Manufacturing, distribution, all that crap. To me, the only reason those people exist is to serve my needs as the sales guy. There are no widgets if I'm not selling
Starting point is 00:14:32 them. So I value the sales person in the head of sales is more valuable to me than the CEO. I can always replace the CEO, but I can't replace a great saleswoman or great salesman because they know not only their product inside out, they know their distribution channel, they have relationships with their buyers or whatever it is. It's all about sales. And so, you know, when I go to a value of company, there's only two people I want to talk to before the CEO. I want to meet the person running social media and I want to meet the head of sales. And I take them out for dinner, separately. We drink really good wine on my tab. Everything goes better with a couple of bottles of wine. You're going to learn a lot more. And then I know two things. What the sales distribution
Starting point is 00:15:24 channel feels like and CAQ and ROAS, customer acquisition costs and return on ad spend. Just those two people will tell you, is this a good business or not? Because if they know what they're talking about, and I know what they, if they know, right away. Yeah. All I'm doing is pouring gasoline on the fire and building the business because they've already figured out the business model. Now, it doesn't mean I whack the CEO, but usually you find out, often the CEO is not the original founder, and they don't have that much stock. It's some guy that found the company that's still in there that's, you know, the engineer
Starting point is 00:16:01 or something. It's very different every time. But sales and social media are really what it's all about. I want to go back to talk about the learning company. So you sold it for $4.2 billion. And later on, the company basically failed after it was bought. And for me, I've got this company at media. I've essentially been growing it for five years.
Starting point is 00:16:26 And selling it really scares me because I know that so much can go wrong after you sell your company. So walk us through, like, would you have done anything differently with that sale? And like, how should we think about exits as? to entrepreneurs. So that's a classic example of failure of meshing two cultures together. The learning company was extremely entrepreneurial. It would do a new title every four months, maybe even every 90 days. And we had a very tight relationship with retailers. Back then, the distribution of software, all software, was on CD-ROMs. Slowly transitioning to online,
Starting point is 00:17:01 but majority of titles, and particularly the gaming side, were all CD-ROMs. And so there was retail distribution and shelf space and purchases online and everything else. but it was CD-ROMs. And so you would go to Walmart or Target or any of the large retailers that had multiple yards of shelf space for their software titles like records. And you'd have a planogram set up for an annual basis,
Starting point is 00:17:22 and you would always hit your target. So if you're going to drop a new version of Oregon Trail, you're going to make 12 million copies. If to manufacture them, you've got a massive logistics problem, you're going to deliver them to every Walmart and every target and everywhere else they were going. And you never missed that, that slot because the retailer was giving you maybe 18 inches of space, which extremely valuable
Starting point is 00:17:44 for six or seven facing skews. And so when we hit Walmart, when we were doing our plans, one of the great advantage was they had these incredible brands like Fisher Price and Barbie and American Girl. And so what we had modeled out in the learning company so successfully is I had a job decades earlier just for the summer, you know, between, my first and second year of MBA, Nabisco Brands, and I worked for a Dutch product manager who had Miss Mew cat food. And it's remarkable how experiences in your life
Starting point is 00:18:22 that you inventory in your brain, that you don't use for a decade, come back and serve you later. I guess they call that experience. Yes. My first day on the job, my Dutch boss basically said, look, you're gonna be here for four months. and I want you to launch two new flavors
Starting point is 00:18:41 so that we can get more shelf space on Ms. Mew. But you should understand something about cat food. There's only two engines of protein. It's beef renderings and chicken faces, which are boiled in papaya juice and compressed, or it's tuna from the sea of Japan, dark, the underbelly of tuna. That is your protein base.
Starting point is 00:19:06 Your job is to dream up a flavor. on one of those two engines of protein. So whether it's going to be bacon bits or egg bits or green pepper, and you call that the flambay or something, whatever it is, because the cats don't have credit cards. It's their owners that buy the flavor. And they say, well, I think Kitty would love that one. And so you have to dream up a flavor.
Starting point is 00:19:30 And I was pretty good at that. But the thing that hit me when I went to the rendering plant to see the two stacks of protein manufacturing, like the face of a cow getting scraped off the skull and getting boiled in papaya juice was pretty fucking freak, excuse my language, pretty freaky. I mean, it really freaked me out and then slabs of tuna. But two engines, it was two engines, and everything else was just marketing. Marketing.
Starting point is 00:19:56 Years later, I'm looking at our business at the learning company and we're, you know, we're growing, but we're lots of competitors. And I said to my partner, because I had a fantastic, because my weakness was, my weakness was logistics, so I found a partner and became partners in the business. I was sitting with one day in the office around six at night in Boston, I said, I want to tell you a story about this trip to the rendering plant and hear me on this, because if you looked at our business, that 80% of it was advancing math and reading scores. So we had math, rabbit, read a rabbit, this title, that title, we're advancing these two scores that parents bought the titles for to advance those scores for
Starting point is 00:20:37 for their children because in school you got to it's math and reading all the tests right so we would advance math and reading scores we were pretty good at it and I said if if those are the two engines math and reading why do we have all these programmers why don't we just get two teams that just do math and reading core code and then we add a license like a you know, Big Bird, or we get, you know, whatever, you know, character we would go license, whatever it was. It was Big Bird. It was the Muppets.
Starting point is 00:21:17 It was whatever it was. And we just slammed it on top of one of the engines. And my argument was our kids are four years old. They don't care if it's the same software. They're four and they're five and they're six. They just want the character. So we can license the character. We can fire two-thirds of the coders, which are really expensive.
Starting point is 00:21:37 and just use the two tuna and beef. That was the moment that changed everything. And he said, I love it, let's do it. And the shit hit the fan. There's even an article in the Wall Street Journal. It's just, no one had ever done this in the software industry, the consumer software industry before. Our cost of capital dropped dramatically
Starting point is 00:22:01 because our margins went up dramatically. And we were so, our valuation was so high, We used our stock to do hostile acquisitions on all our competitors. We ate them alive, and we fired all their programmers, and we just licensed our characters. And we dropped our prices by 50 percent, and we increased our volumes by 5X. We took the software business down from $99 to $1299, and we were profitable. All from that magic moment with that Dutch product manager showing me beef and two. tuna. I owe so much to that guy. But that's how life is. It's serendipitous. You don't know
Starting point is 00:22:45 the moment that's going to change everything. We commoditized educational software. We sold hundreds of millions of copies of it in multiple languages all around the world of the tuna and the beef. That was it. Yeah. And, you know, so when we tried to integrate that philosophy, going back to original question. I said to the CEO then, look, we're going to have to get the Barbie title out in 90 days. We don't need anything. We're going to do it off the tuna and beef. She said, no, no, no, no, we're going to have to study this for two years. I said, no, no, we're going to study it for two minutes because we have an order for 12,000 units the first day, and 12,000 the day after that, and 12,000 the day after that, it's the holiday. We're putting it in for September.
Starting point is 00:23:34 we've got $24 million worth of orders here just on the Barbie reading title and then we're going to do the American girls title same thing and then we're going to do the math reading American girl it didn't matter to me but the philosophy there was completely different that these were very coveted brands
Starting point is 00:23:53 and I understand it but the amount of money we left on the table the profit margins on just putting our own character onto a title our margins are like 70% So we gave up hundreds of millions of dollars, and that is what I call a cultural error, because I didn't control the board, although I was one of the largest shareholders. And I went and saw the board, said, guys, this is nuts.
Starting point is 00:24:20 But it put me in a conflict with the management there. But I lasted quite a while, explained to them how to do it. And unfortunately, it didn't work out for them because they went and said, no, no, no, let's wait two years. Two years, it's over in the software business. We left hundreds of millions of profit on the table. Hey, App Bam. Launching my LinkedIn Secrets Masterclass was one of the best decisions that I've ever made for my business. And I didn't have to figure out all the nuts and bolts of creating a website for my course.
Starting point is 00:24:47 I needed a monthly subscription option. I needed chat capabilities. I needed a laundry list of features to enable what I was envisioning with my course. But here's the thing. All I had to do was literally lift. a finger to get it all done. And that's because I used Shopify. Shopify is the easiest way to sell anything, to sell online or in person. It's the home of the number one checkout on the planet. And Shopify's not so secret secret as shop pay, which boosts conversions up to 50%. That means way fewer
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Starting point is 00:27:13 Restrictions apply. Services not available in all areas. So I know that you were essentially in this business for over a decade, right? Oh, yeah. Once you were out of the business, I know they bought you, you were still working in there, but once you were actually out of the business, did you have any sort of like identity crisis? Did you go through anything mentally? Well, I had a non-compete for 36 months.
Starting point is 00:27:34 I was getting my full salary, although I think that's illegal today, but back then it wasn't. And so I said to my family, look, why don't we go visit every beach on earth? Let's make it a mission to go to every great beach on earth just for the hell of it. And after about 90 days of doing that, I was bored out of my mind.
Starting point is 00:27:53 I just said, what am I doing? This is crazy. I'm not in the game. And so I immediately said, okay, I talked to my lawyer, I said, what are the confines of this non-compete? I don't want to get into litigation. What else can I do? And he said, well, you can be an investor,
Starting point is 00:28:13 and you can start investing in startups, and you can go on boards, and you can, I immediately said, okay, I'm going to do real estate. And I started doing that, and I got into climate-controlled storage, and I started to diversify into all, 11 sectors. And, you know, my operating days were over and my investment days were starting. And I was going through a transition of from being the, you know, the operator guy to being the investor guy.
Starting point is 00:28:43 And how old were you at this point? I think I was 36, maybe 40, I don't, around then. And I was, you know pursuing my passions watch collecting um i was always a film editor and i wanted to keep my chops up and i was still cutting on an eight-plate steenbeck things like that um and and that then all of a sudden i started having some failures and successes on the investment side and so i was starting to understand you know i was starting to identify people and being able to read their trace to determine which one's the back and which one's not to, which I've become, I think, very good at.
Starting point is 00:29:28 And, you know, I can see the ones that have what it takes. But it's really from the experience that I learned during that time. And life got even more interesting because today, you know, in an average day, starting for me at 545, because I was riding my bike on Miami boardwalk, along with a lot of other people do the same thing at sunrise.
Starting point is 00:29:53 And I'm listening to all of my messages or the feeds of the networks. I listen to BBC, Al Jazeera, Fox News, Fox, NBC, all of them. I just listen for the seven stories of the day because I'm often going back on those networks and doing my contribution. The phone will start ringing. And in any one-hour cycle, there will be a phone call of utter catastrophe,
Starting point is 00:30:17 just got sued for $100 million, you know, product food poisoning or something in the product line of the company I'm invested in, whatever, something catastrophic. Minutes later, total euphoria. I just got an offer to be bought up for a quarter of a million cash, and you're, you know, crowling shareholder, are you going to agree with this deal or not? I'm thinking to myself, you have to learn. how to be, what's a great word for it, you can't get emotional about this stuff. It's like stoic.
Starting point is 00:30:56 You just have to realize that for every catastrophe, there's euphoric outcome. And by the end of the day, your life is balanced again. So I just wait. I wait for the bad news. I wait for the good news, and I just roll with it. And I found it very, very interesting to see how that plays out. And our portfolio is now 54 companies, plus a bunch of other stuff we do. but I will say that that was quite a journey to understand how that works because you can hit me with,
Starting point is 00:31:30 I mean, people, you're getting sued or something, I don't give a shit. Like it just, you know, people that sue me and I get a lot of litigation, these are, you know, there's contingency lawyers, I always say to them, go back and look at the last 30 lawsuits and show me, can you outlast me? Because I know how you work. You're a single-cellamiva contingency lawyer. You're only going to be able to hold this up for seven years, and I will outlast you. And your partners will say, we've got to give up on this guy. But you should know that now. Because, you know, I got a lot of this crap. It's one of the bad things about the system. But I left to
Starting point is 00:32:17 with them. Yeah. I really like to fuck with them. It's really powerful what you're saying. You're saying, like, don't, you know, get too excited about the highs. Don't go so down when there's anything bad happening in the lows. So for new entrepreneurs, that's really difficult. Like entrepreneurship, sometimes it can feel like you're just getting punched in the face over and over again. And sometimes it can be really good. But how can we better manage those highs and lows? What advice you have? It's important that you get punched in the face. It's important. It's important. that you get bloodied and get knocked down multiple times, it will never be an easy ride, ever, no matter what you think. And no matter what you think your plan is, it won't be that
Starting point is 00:33:00 that works. It just never is. And so really what the punch in the face is teaching you is how to pivot. And the more you get beaten to a pulp, the better it gets. Because you start to realize, if I go in that direction, I'm getting another smack right in the face. I'm going to go in this direction. It's less painful. It's sort of trying to figure out the path of least resistance based on your experiences of what didn't work. But I have never met anybody that's been successful ever that said it was easy, that ever said they were able to take their original business plan and execute on it because that never, ever, ever happens or didn't go through hell on earth to get to where they are. And so only one third of the population can, you know,
Starting point is 00:33:46 and do it. That's it. And I'll tell you a story that I think is very important that I always bring up for everybody to think about. We talked about business school. You and I have both been there. In my last week in the second year, they were getting, you know, Jamie Diamond kind of guys would come in and lecture about their sector and, you know, people are going to go work in financial services or whatever. And this guy came in. I'll never forget it. Never. I mean, it's probably the only one I'll ever remember of all the guests we had that week. And he didn't say anything for like a minute and a half. You know, the amphitheater type thing, it's a staircase up the sides,
Starting point is 00:34:24 and you got 240 people sitting in this thing and got the nameplate in front of you. He just looked at everybody for the most uncomfortable period of time. And then he finally said, oh, MBAs, you think you're so damn smart. And you're just going to get out there and kick the world's ass, and you just can't wait to leave here. Well, let me tell you what's really going to happen to you, people. A third of you are going to become consultants and leave a life of mediocrity and never make a decision of consequence in your life and eventually go to consulting hell when you die. Because it's true about a third of the class we're going to become consultants. And they were going to lead of life of mediocrity and never make a decision of consequence.
Starting point is 00:35:18 They were just going to be consultants, which is such a waste of a life. And then he said, a third of you think you're entrepreneurs and you're going to try and you're going to fail over and over and over again until you're an employee again because you don't have what it takes. Very depressing. And the third, he said, are going to work like hell for much longer than you think. and you will make it but it will change you forever it's so hard and I leaned over to Barry
Starting point is 00:35:49 my guy beside me I said this guy is such an asshole but today that guy is me because when I meet my new cohort I give them the same speech because he was right
Starting point is 00:36:01 he was 100% right and so it's sort of you learn that as time passes that the journey for entrepreneurship is into the valley of death. It has to be, or you will never be successful. And when you get out of the valley of death and you all of a sudden have your five-mill in your T-bills
Starting point is 00:36:22 and you're working even harder than you started because you're trying to do something else. Entrepreneurship is a disease, actually. It's a virus, and it never sets you free. And so you have to know that, and the more successful you are, the harder you work. It's never, you're never going to be free. And then you have to decide, what's my life balanced like?
Starting point is 00:36:41 Well, there isn't any. It's a bullshit concept. It's bullshit. The idea, oh, I'm going to have time for my family. That's such shit. That's a bullshit. You might as well face it. You're going to work like hell.
Starting point is 00:36:53 And as you grow a family, you better have a better significant other that can take time to raise them because you won't have any. And I know that sounds like a sacrifice because it is. But you will buy your family freedom. That's what you will do. Now, do you feel like some people are not cut out for entrepreneurship at all? And do you feel like there's some people who can be, you know, some people are natural entrepreneurs. I think you're a natural entrepreneur and some people can be taught.
Starting point is 00:37:21 What are your thoughts on that? I think you have to have certain personality traits that, I mean, for me, it's marketing in sales. Other entrepreneurs have great technical skills or whatever. Everybody has something that they are particular. fairly good at, it's in their DNA. But there are attributes you learn over time because you're getting punched in the faces
Starting point is 00:37:42 you brought up earlier. These are important lessons that give you ammunition for the future, not to make those mistakes again. There are some lessons, and I've talked about this quite a bit lately, that I find very, very important that I have to share with you because everybody should listen to this. When working for jobs, for Steve Jobs in the early 90s, he, not a nice guy, that's well documented,
Starting point is 00:38:15 but he had a concept that I'll never forget, and I used it and it really works, and he changed me forever with this. He said in any day, in any 18-hour working day, because he worked 18 hours a day, the guy was unbelievable. What a ferocious guy. I mean, damn. You never met anybody like it, but I hadn't anyways. He said there are three things you have to get done in this one 18-hour cycle.
Starting point is 00:38:43 That is called the signal. Your ability to know what the three things are is what you must learn. But once you know what the three things are, that is the signal. And all the things that will happen that stop you from getting the three things done is the noise. Yep. And the ratio must be 80% signal, minimum, 20% noise, or you will fail. Wow, was he right. Yeah.
Starting point is 00:39:10 And so if you can learn to do that, nothing could stop you. Unfortunately, one of the problems with this strategy, as you will find, is you will have no time to suffer fools. You don't have any time. So if somebody comes at you with something that's clearly noise, you don't have any time for them and they take it personally yeah i don't give a shit because what i've learned is they will come around when they realize that you're achieving your goals and you're executing they will stay part of your team because they want to be led by somebody
Starting point is 00:39:51 that gets it done and wins and you can only win if you understand that you must get the three things done. You don't need friends in business. You need people that respect you. I'm trying to teach this. You don't need to make everybody happy because you can't. It's impossible. You want to make your friends and family happy, which is probably no more than 15 to 20 people that matter to you in your life. Everybody else is either noise or signal. And you have to treat them that way because that's the right way to treat them. That's the fair way to treat them. That's what helps them get their job done. And I go through this every day.
Starting point is 00:40:30 Now, the only guy that I've seen that's a higher ratio than jobs was is Elon Musk. 100% signal will not waste one nanosecond on noise, which makes him very awkward socially. He'll walk away from conversation two seconds the minute he knows its noise.
Starting point is 00:40:48 Really? So if you're not contributing towards getting something done, see you later. Ask anybody that works for him. But boy, do they want to wait? work for him because look at the success he's achieved. People want to follow a successful leader. So as an entrepreneur, your job is not to make everybody happy.
Starting point is 00:41:07 You will fail. You can't make everybody happy. You want to respect people. You want to honor them. And you want their respect, but don't try and make them happy. Not going to work. So you mentioned earlier that you've invested in 52 or so companies. You obviously have been on Shark Tank for a very long time.
Starting point is 00:41:28 You know what successful founders look like, what entrepreneurs that are really successful sound like and all their different traits. So I thought we could play a fun game called Rate the Traits. And basically, I'm going to list off a trait about entrepreneurship, and you're going to let me know, is it a 10, is it a 1 through 10. We'll rate them 1 through 10. 10 is a high score. Got it.
Starting point is 00:41:50 I'm interested. I'm interested. All right. So we're going to rate them 1 through 10, 10 being really needed for. successful entrepreneurship one being not so needed okay first prompt creativity 10 why that's problem solving that's when you get punched in the face if you don't have a creative bone in your body you're just going to keep getting punched in the face you got to think outside of the box that is a definition of creativity you have to realize out that hurt i don't want another punch like
Starting point is 00:42:21 that, how am I going to solve for that? That is using the brain. Okay, next one. High risk tolerance. I'm going to give it a five. Risk tolerance can also be stupidity, doing things because you, I can take the risk, I can take the risk, and keep failing. You're an idiot. I mean, the whole idea is to mitigate risk. In fact, I'm going to give it a one. Don't do stupid stuff. Don't do it. Don't keep risking it all over and over again. The whole idea is to find the path of least resistance without the risk. But it's true that when you launch, you're taking huge risk. But as you build it past the first 100,000, you want to stop taking the risks and start to mitigate the risk. So it's the launch itself, you need some
Starting point is 00:43:17 cahunas. Because most people say, I don't want to do it. I'm not going to do it. You have to try, even though you're going to fail three times at least, probably. But you only need one hit to make it to get your five milsky. Yeah. Okay, being able to tell good stories, so your storytelling ability. 10. 10, 10, 10, 11. The world's changed so much that if you can't tell the story of your product or service, if you can't capture someone's imagination about the promise of your brand, you will fail.
Starting point is 00:43:48 storytelling is the whole deal because we are living in a social media customer acquisition cost model now for large and small companies great storytellers people that can capture the audience capture the potential customer bring them into the aura of the promise of the brand these are great entrepreneurs these are great social media directors these are great editors storytellers videographers, photographers, they tell stories. And you know what, I'm going to give it at 15. That's how much I feel about it. Wow. Charisma. Not important. I'll tell you why. I do business and invest in a lot of assholes that have no charisma, but they have remarkable executional skills. Charisma can be also bullshit. You know, you want sexy charisma. You show me executional skills. That's
Starting point is 00:44:47 sexy. The fact that you can set a goal each quarter and hit it, that's charisma. So, you know, traditional definition of charisma is bullshit when it comes to being an entrepreneur. Industry experience. Yeah, I'm going to give it an eight, and I'll tell you why. There's a concept developed in Europe decades ago, hundreds of years ago, in places like Switzerland and France, Germany, Italy, where they create apprentice programs, where they bring talented as young as 14. And they let them work for a stipend and a free lunch or whatever after their school at four o'clock till seven at night so that they can experience what it's like to work in a business and understand what the passion is of that business whether it's watchmaking or pharmaceuticals or tire making
Starting point is 00:45:35 or high-end machinery in switzerland whatever it is to see if they have the attribute or the DNA to connect with what that's about particularly important in the watchmaking industry when they identify you to be a master watchmaker when you're 14, you're going to commit your whole life to it. I know a lot about that. And that's industry experience, but at a very early age, so you can find out, do you connect with the cosmos of that business? And is that your path for your life? You don't know until you try. Okay, last one. Failing fast. Yeah, that's a buzzword in the valley. I don't put a lot of weight on. I'll tell you why I'm going to give it a two, Here's the rule that I've put in place.
Starting point is 00:46:19 In your launch years in your mid to late 20s and you've decided you're gonna pursue the entrepreneurial path, one of your most important assets is time. So, and I've seen this countless times with entrepreneurs, I meet them in their fifth year of beating a dead horse that just never took off, but they're so emotionally attached this piece of shit idea that they're going to bankrupt their parents to mortgaging their
Starting point is 00:46:51 parents home. I mean, I've seen it so many times. If after 36 months, it's not working. And by working, I mean it's growing and it's profitable. And you clearly have figured out how to acquire customers. Take it behind the barn and shoot it. I'll do it for you. Good bottle of wine, shoot it behind the barn because it is killing you. It is sucking your energy. It is sucking your and it is basically taking away from the most valuable thing you have, the time to start a new idea. Entrepreneurs deal with failure. They have to, because they're going to fail.
Starting point is 00:47:29 There's no such thing of just starting something out of the basement. It happens so rarely that it won't happen to you. I can tell you that. You can't, I prefer to shoot them after two years. If in 15 months, they haven't figured out CACC, Customsac, they're going to fail. Yeah. And why spend any time on a dead idea that didn't work?
Starting point is 00:47:54 It's okay. It didn't work. Who gives a shit? Move on. I much prefer to invest in entrepreneurs that felt the sting of failure, but understand. So, you know, fail fast. If it means take it behind the barn and shoot it early, great, but shoot it. And don't let anybody tell you, you know you've got to keep on going and wasting everybody's
Starting point is 00:48:13 time and money. Because remember, the people that you're employing, You're also hurting them. You have a responsibility to tell the truth to them and say, look, this idea didn't work. I'm going to fire you with his best package I can give you, but I'm also starting something else. You get a lot of respect for that. You really do to admit failure and own it. And the thing that drives me crazy about people, and I'm telling you to listen to this because I get pitched a lot.
Starting point is 00:48:44 and I say, well, what did you do before this? What were you doing in the last two years? And they talk about a business, and they tell you it failed, but it wasn't their fault. They'll tell you every reason on earth why it wasn't their fault. Bullshit. They should own it. It's 100% their fault. They were the founder and the CEO.
Starting point is 00:49:08 It wasn't anybody else. They are the person who failed. Unless I hear that, I never invest in them. There's so many people that want to believe. Oh, the market changed. Oh, the competitors changed their prices. Oh, there was dumping on the market from China. Yada, yada, yada, yada, yada, yada, yada, yada.
Starting point is 00:49:26 Bullshit. They failed. So accountability. A hundred percent. And some of them walk away in tears. When I forced their nose into, you know, when a puppy takes a shit in the house, and the first time you're going to roll up a newspaper, stick is no. nose in it, give them a little whack. They never shit in the house again. I stick their nose in their
Starting point is 00:49:49 failure and I whack them with a newspaper and say, this shit is your shit. You dumped this. You failed. Now smell it. That's what has to happen. Well, that was a fun game. Is there any other traits that you want to call out that you think makes a good entrepreneur? Yeah, I'm going to give you some interesting points that I learned, you know, after all this time and investing so many different people. And after, you know, a few years, I start to see which ones are successful, and I look at their traits. And let me give you some. Remember, these are in different sectors. They don't know each other, different businesses completely. And yet they're successful versus ones that are not so much. Because even in a venture portfolio like mine, maybe three
Starting point is 00:50:33 out of ten really work. And what do you consider a successful business? Like how big do you have to grow? before you can well you know what you're the classic venture capital model is if you invest in 10 deals five years later two have gone bankrupt um six of them are living dead just sucking your time they're not going anywhere they should be shot behind the barn but they won't shoot them and two of them made a thousand X and they paid for all your mistakes so you know as an investor you want to focus on your winners and you got to figure out which ones are losers and winners we a little bit better on Shark Tank deals because we have 110 million eyeballs seeing the product and syndication, so our customer acquisition costs are lower. So call it three to four out of ten work.
Starting point is 00:51:17 So even a marginal business works on Shark Tank. One of the reasons you want to get on Shark Tank is that free eight minutes of network television on in perpetuity and syndication. Ask any entrepreneur, their product just keeps showing up on television every night. It's pretty good. And so we want to invest in companies like that. But what happens is, You look at the traits of those people in the winners. Let me tell you what they are. Very boring in some ways, but you'll find this fascinating. Number one, this may sound crazy, but it's true.
Starting point is 00:51:49 Diet. Somehow, along the way, they've decided that food is important to them. Not some crazy Atkins diet, none of that stuff. The rule that I learned from two of them, and they didn't even know each other, was they look at their body weight. Let's say they weigh 150 pounds. they eat 150 grams of protein a day, one gram for each pound, which is very hard to do, by the way.
Starting point is 00:52:13 Very hard. But you don't have to modify your diet that much. You just have to decide what you're eating and it has to be more protein-based. There's lots of ways to do it. There's lots of apps you can lose it. It's free. Just take a picture AI tells you how many grams of protein
Starting point is 00:52:26 in the serving and it just adds it up for you during the day. And the other app that I use because I'm doing this myself now is Yuka, Y-U-K-A, scan any snack, and it tells you a score from zero to 100. anything lower than 60, don't put it in your mouth. After about 10 weeks of just following this protocol, your energy level goes through the roof. It's unfitting real, how good you feel.
Starting point is 00:52:49 That's number one. Number two, the classic exercise. All the entrepreneurs that are successful have found a way to spend some portion of the day exercising. Sometimes it's only 10,000 steps a day, that's it. I do cycling. Those two together kind of... This one is really interesting.
Starting point is 00:53:07 See, I'm wearing an aura ring here. I got into this about four years ago. A great entrepreneur showed me this product was more of a prototype back then. Sleep. You know, decision-making and critical thinking and sleep go together. So you really want to try and figure out sleep,
Starting point is 00:53:33 and it's not just any sleep. These rings and these other devices, there's many other devices. break down your sleep into the REM sleep and the deep sleep. You want REM sleep. That's your brain being cleansed for the next day. Unfortunately, sleep doesn't work with alcohol. And this is a big problem for me.
Starting point is 00:53:55 I don't drink, I mean, sorry, I don't smoke, I don't do drugs, but I love wine. And if you drink wine three hours before you go to bed, you don't get any REM sleep. it really your sleep so the strategy you got to go to is drink at breakfast and don't drink again
Starting point is 00:54:16 because at the end of the day if you can get those seven hours the sleep, the diet and the exercise you can't believe how you feel as an entrepreneur you need that energy
Starting point is 00:54:29 and you're going to get it and most of my entrepreneurs are hip to this now and are struggling with the whole wine or they're moving to the purest tequila or something where they don't drink it before they go to bed or they don't drink three days a week or whatever it is everybody's trying to solve for this alcohol problem because all the rings are showing you you get no rim and one last one
Starting point is 00:54:47 and this is the one that that I really have learned and you've got to try it entrepreneurs once they're successful or the business are growing their business get in a rut they only want to do things that give them a good outcome because they've been trained of the punch in the face so many times that they get into this routine of only doing the things they know well over and over and over again all day long and it's easy to get there particularly when the team is humming sales are coming in everything's going great but the one most important exercise you're not getting is that on your brain because you're now in the maintenance mode and that's not where great creativity comes from so you have to get into a position and this is very very difficult but i've done it and
Starting point is 00:55:46 believe me it works and i learned it from one of my great women CEOs years ago she said you've got to spend a portion of every day outside of your comfort zone in some space that you're very nervous about getting into because you're scared you're going to fail and you're going to be embarrassed in front of your team or in front of your family or you can't do it or you don't think you can do it it could be learning how to play the cello it could be painting it could be mahjong or something or chess or it doesn't matter it's something you don't know how to do that you're forcing your brain to deal with and the uncertainty this gives you a superpower because you're basically recharging your ability to solve problems that you have no idea how to solve.
Starting point is 00:56:35 And 50% of the time, you're successful. This is the superpower for really good entrepreneurs to do. And yet, no one wants to do it because, oh, I don't want to be embarrassed. So I'm telling you the story because last year, I got a phone call for one of my agents, And he said, listen, Kevin, have you ever heard of Josh Safty? He said, yeah, that's the guy that directed Uncut Jams. And Ronnie Rothstein wrote it. It's a great movie, Adam Sandler, dark comedy.
Starting point is 00:57:09 He said, he's making a new movie called Marty Supreme, and they're looking for a real asshole, and they think you're it. I said, I don't act. He said, yeah, I know that. And I'm just telling you, if you're going to pursue this, you could shit the bed and destroy your brand. you could look like a real dick. But that's when it hit me.
Starting point is 00:57:30 I got to do this. I got to try it. I got to see if I can learn 70 pages of script. How do I do that when I'm dyslexic? How am I going to memorize all that stuff? I said, do it. Just see what happens. We finished it a few weeks ago.
Starting point is 00:57:44 It had some screenings. And the buzz for Timothy Chalamee. So it's Timothy Chalomey, I'm Gwyneth Paltrow's husband. It's a movie from the 50s. Amazing. Yeah, it was shot in New York and Tokyo. And the experience was remarkable. But the buzz for that movie, and this has really not that much to do with me because I'm just a supporting actor, is Oscar.
Starting point is 00:58:11 So I would love that thing to win. I'd like Timmy to win one. I'd like the director to win one because that would be great for my little contribution in that. But I worked on that for eight months. And it was totally outside of my comfort zone. So I'm waiting to see what audiences think when they see me in it. So go see that movie Christmas Day. Amazing.
Starting point is 00:58:30 You know, Marty Supreme. But the point is, do something today outside of your comfort zone, whatever it is, because you're not doing that. I know you're not doing that. No one's doing that. And it's a superpower. What do you feel like you learned from, you know, you were in this movie. You weren't just like a little blip at the movie. It sounds like you were in it.
Starting point is 00:58:49 No, I played a role as the richest man in America. married to, you know, in a loveless marriage with when a pouch, it was very dark. I'll tell you what I learned, and I could have never known this until I was in the moment, when you make a movie like this, particularly a period piece, and you have a great director like Safdi, what he wants to do is create an environment with like 100 extras, and we took over the Plaza Hotel from 7 at night to 7 in the morning. And I'm just remembering this one sequence we shot all night long. When you close your eyes before he says action and everything on the table is vintage 52,
Starting point is 00:59:30 your clothes are 52, your watch is 52, everybody, the menu is 1952, the art is 52, everything around you is 1952, all of a sudden you magically transformed to 1952. You're there, you're in it, and everybody is in 1952. And it's not, you're not acting anymore, you're just there. You're just being your character in 1952 with everybody else in 1952 and magic happens and by the time you do the 40th take
Starting point is 01:00:00 you are definitely in the zone because you're doing it on film and they have to move the single camera back and forth and you're there all night long. I remember that day in New York when that day was over it was a very, very important scene which if you see the movie
Starting point is 01:00:15 you will definitely remember this scene. It's dark. It's dark. But I was so wired when I got back to Casa Chippriani's in New York where we were staying, my wife and I, it was 7 a.m. And I went upstairs to the restaurant and I said, look, I want the scrambled eggs and I want some smoked salmon. And I want a 1922 or 22 bottle of Montresche.
Starting point is 01:00:43 You said, sir, it's 7 in the morning. I said, not for me. I just got back from 1952. I need a bottle of Montresche. And I called my wife, said, look, I'm drinking up here. She said, what are you crazy is breakfast? I said, no, I'm just so wired. I'm just so stuck in 50, too.
Starting point is 01:00:59 I got a snap out of it. It's like, if you're dyslexic, sometimes the world will shift 180 degrees, and you have to shake your head and get back. It snaps back. I was in that kind of a mode. I had to get back to 2025, and I didn't want to go back to 2025. It was so magical to be in the birthplace of entrepreneurship in 1952 in America, because that's where the American Dream started in Brooklyn back then.
Starting point is 01:01:23 And that's what the movie's about. And so I was, I mean, it was emotional for me. It was crazy. And damn that Montreschet was good. That's how that experience was. And it comes out Christmas Day. I can't wait to see it. I mean, I'm so proud of the work.
Starting point is 01:01:38 I mean, I just dying to see what people think. Okay, let's switch gears back into your investing in other companies. I learned that you only invest in profitable companies. That's not quite true. The larger investments, that's astute on your part, if I'm going to put in $5, $10, $15 million, it's into a business model that's proven it's profitable. And I'm just negotiating my liquidity, my position on the cap table, what I bring to the table, what my team brings, it's a negotiation. That's really the majority of what I do. But I also have a massive, you know, I feel that all of us on Shark Tank can become ambassadors to the American Dream.
Starting point is 01:02:18 And so we invest in many, many, many startups. And my job is to figure out, you know, which one's to back. But I have learned something about this whole Shark Tank journey that goes to this point. I always thought a decade ago that, you know, people thought of America our number one exports probably technology or energy. It's not, it's the American dream. That's what we export. And Shark Tank's just part of that whole thing. The number one thing that we export around the world is the idea that you can start
Starting point is 01:02:48 with an idea and change your life forever with it. So that's what Shark Tank's about. But most of my larger investments are, as you suggest, they're in profitable companies. My job is to make them more profitable. But I also do my own startups outside of Shark Tank. Recently, I just did WonderCare, watch insurance for people that own watches.
Starting point is 01:03:11 Because if you put it on your home package, you may find this out the hard way. Many home package insurances with a rider for watches of jewelry. They give you the depreciated value. Watches do not depreciate. Rolex goes up in value over time. So you want to get the replacement price. So that's what we offer at WonderCare.
Starting point is 01:03:26 To do that business, I partnered with seasoned professionals on the tech stack of AI to be able to scrape insurance data so we could issue policies through AI. Wonderful relationships with companies like Chubb. You know, I'm one shareholder in it. I think I'm the largest shareholder because I funded it from the beginning. but I probably won't end up remaining the larger shareholder because I'm going to bring a lot of talent and we just hired a new CEO.
Starting point is 01:03:53 And it's growing. Business is growing. And so that's from scratch. And I'm very fortunate as you are. I have millions of followers, millions of followers, and they all know I'm a watch guy. So my customer acquisition cost is zero. I just do my own 15 second ads on my own social media
Starting point is 01:04:12 and I say, look, I'm selling this product. I use it myself. and here's why, and I'm fortunate enough to issue policies without any customer acquisition cost. I don't know anybody else in the insurance industry that has that luck. So you're bringing up a topic that I feel like I talk about on almost every show now, which is creator entrepreneurship. I feel like that is totally the future. Having a personal brand is so important, especially with AI coming out and just the ability
Starting point is 01:04:40 that it's like everybody can start a business, but what is actually going to differentiate you? And I think what it is is your ability to create content and grow on social media and be a creator-entrepreneur. What are your thoughts about personal brand and the importance of it as an entrepreneur? You're more than 100% right. You are more than 100% right. It's the greatest opportunity this economy has ever offered an entrepreneur. It's extraordinary.
Starting point is 01:05:05 But it goes back to something you said earlier, storytelling. If you don't have the ability to tell a story, you can't do that. Personal brands are built on remarkable, authentic, passionate relationships with communities that you're building. People smell bullshit a mile away on social media. If you're not authentic, if you're not honest, if you're not telling the truth, you're going to get slaughtered, beyond canceled. I mean, so the brands that are working are the ones that say, look, here's what I am, here's what I do. This is the way I see it. You may not agree with me, but I'm always going to.
Starting point is 01:05:42 to be true to what I believe in, and whether it's a product or a service, the people that fail at this think that somehow they can attach celebrity to any product and sell more of it. People smell that bullshit so far away. The only products I ever associate myself with, I eat my own cooking. I would never, ever endorse a product I don't use, ever. I get offered that all the time. Well, we'll pay you to say this is great. I don't know it's great. I'm not using it and I never would use it. You know, it's just not what I want. It's not an easy path, but when you start what you have on your, if you're good at it and a good storyteller and you're authentic, you get advocates. They become your community. They tell others about how important their
Starting point is 01:06:32 relationship with you is. And that is a remarkable outcome. It is the ultimate ultimate entrepreneurial experience. I'm part of this entrepreneurship group called Hampton, and there's like 10,000 of us and a Slack channel all across America, and I'm probably one of the only, like, real creator entrepreneurs, and I find that, like, I don't relate to them at all.
Starting point is 01:06:57 Like, I don't relate to them at all because I feel like all their problems, for me, it's like I'm coming out with a new LinkedIn offer that's going to be for small business owners. And to sell it, like I just, have the idea and I'm just going to, you know, put it online and run a couple webinars and I'll be sold out, basically. And so, like, it's just, like, so simple. I have an idea and I just put it out and, you know, operationalize it. Well, that's because people trust you. They know who you
Starting point is 01:07:23 are. I mean, it's all, these communities are built on trust. They're built on a someone who believes what you said and believes you will deliver what you say you're going to deliver, and the experience will be a positive one. And if they buy or use the product again, second time, they will experience the same they did on the first. That's a brand being built, and that's what the whole deal is about. And you can't do that unless you're authentic and you deliver what you said. It's why the bloom is off the rose on a lot of celebrity endorsements now, because they're not being transparent and honest. They don't actually use the product. I mean, you can't endorse 16 products. You possibly can't use them. The model's changing. That's why
Starting point is 01:08:04 you can emerge as a creator out of nowhere because you're authentic and all of a sudden have, you know, 10 million followers that believe you. I think it's a great and powerful force, but also as a dark side. Look what happened to Bud Light. They did that themselves. They didn't think about who their customer was. And they shot themselves in the foot multiple times.
Starting point is 01:08:26 They stored billions of dollars with a market cap. I mean, it was unbelievable. That's the dark side of social media, but shows you the power of it. One of my weaknesses, I would say, is that I'm not the best at finance, right? I have a business partner who does, like, a lot of my finances. And I know that you mentioned one of the things that you see entrepreneurs fail at is not knowing their numbers.
Starting point is 01:08:48 Yeah, it's a big problem. So what would you say are the key metrics that founders, CEOs should be following for their business? If you don't know your numbers, you better get somebody who does, as you've done. You have to have somebody that gives you the dashboard of your business every day. I mark to market my business portfolio, all positions every day, right after 4 o'clock. And I work with my finance team to say, okay, there's something happened over here, something happened over here.
Starting point is 01:09:13 I see this cash came in this account and this bank. What was that about? Because I don't recognize that revenue stream. You know, every single day, I spend maybe 20 minutes just going through the top line of where I'm anticipating revenues coming in from whatever business, whether it's a royalty or whether it's a stock that's going public
Starting point is 01:09:31 or whatever it is every day. And what I find is that keeps me sharp and it keeps me in touch with the ebb and flow of revenue and margin and free cash flow. And so that's what I focus on. If you don't have that skill, you need somebody who has to have, that has it,
Starting point is 01:09:45 because that's a really big problem if you don't do that. And I think, you know, you will fail if you don't, if you can't read. I saw that you were just looking at your watch and I noticed you were in two of them. I am.
Starting point is 01:09:58 This is actually New York time, and this is local time. So I'm in my show with two questions that I ask all of my guests. The first one is, what is one actionable thing are young improfers can do today to become more profitable tomorrow?
Starting point is 01:10:10 Learn AI. Find out which models you can rent for your business, because there is plenty of product on the market now that will enhance your margins and your productivity. Every single one of my companies now is using AI. Most of it primarily for content generation, but they're also using it for all kinds of analytics and data scraping. It's very inexpensive today. Every single one of them is using it. And so if I'm looking at business and they're not using AI. I mean, it's not that complicated. It's very easy to adopt it, and you will find ways to save money almost immediately. I mean, some of these models you can rent for $129 a month that do incredible things with content. So save yourself a ton on creating content for your social
Starting point is 01:10:53 media. And what would you say is your secret to profiting in life, and this can go beyond finance and business? I would say going back to focus on the signal. My secret is I'm able to focus on the signal now every day. I know what signal. I know what's noise. I don't let noise slow me down. And, you know, that's why they call me the mean shark. That's complete bullshit. I just tell the truth. But I'm focusing on signal there and I'm determining what's important for me and the things that matter for that day, that just that day, just the three things that day, it's not that complicated. Not next month, next year, whatever. It's that day. What do you got that I got to get done? I'm going to get it done and I do it day after day after day after day and the more confidence you build and then
Starting point is 01:11:41 I'm really into this mantra of getting up in the morning feeling good because the diet and the exercise and the sleep it's such a game changer you know that old mantra but you sleep on the sofa you only get two hours sleep because you're that amazing entrepreneur that is such crap the guys that are winning and even bezos talks about this he doesn't make big decisions afternoon he doesn't want to be tired he does the sleep thing he does the diet thing he does the exercise thing, and you want to make those decisions. I can even think last week I was riding the bike. It hit me.
Starting point is 01:12:13 I had an idea, and boom, I had that thing executed by four in the afternoon. And it's, I think it's going to make me a ton of money. Yeah, I love that. Kevin, thank you so much for your time today. I really appreciate it. Where do you want to send everybody to? I know that you're so visible online, but where do you want to send everyone to? I'm on all the platforms at Kevin O'Leary TV.
Starting point is 01:12:33 Come and see me anywhere. I love my community, and we have a lot of fun together. And I love the discourse. I love to get into the bait with people because there's always a pro and a con to everything. And I think that's what's great about life, that we have a great discourse. And we chart the path.
Starting point is 01:12:51 I support entrepreneurship in America. We create 72% of the jobs. That's my army. Thank you, Kevin. You're such a role model. Thank you for all that you do. I know me and a lot of entrepreneurs really look up to you.
Starting point is 01:13:03 So thank you so much so much. I appreciate that so much. Take care. Well, guys, this was such an important interview for me. It was a full circle moment because I've admired Kevin for so long and I grew up watching Shark Tank together with my family. One of the takeaways I found most powerful today was Kevin's signal versus the noise framework that he learned from Steve Jobs. Every single day has three critical tasks that will actually move your business forward.
Starting point is 01:13:26 That's your signal. Everything else is noise. The ratio must be 80% signal, 20% noise or less. Or else you'll fail. This isn't just productivity advice. It's a complete mindset shift. Stop trying to make everyone happy. Stop wasting times on things that don't matter.
Starting point is 01:13:41 You don't need friends in business. You need people who respect you. Kevin also reminded us that getting punched in the face is essential to entrepreneurship. Every stepback teaches you how to pivot smarter. But here's the brutal truth. If your business isn't profitable after 36 months, take you behind the barn and shoot it. Your time is your most valuable asset, especially in your 20s and 30s. Own your failures completely.
Starting point is 01:14:03 No excuses about market conditions or competitors. The moment you can smell your own failure and accept it, that's when the real growth begins. And I loved Kevin's emphasis on fueling your body for peak performance, one gram of protein per pound of body weight, consistent exercise, and seven hours of quality sleep. These aren't just wellness tips. They're competitive advantages that sharpen your decision making when the stakes are highest. Remember that Kevin said, entrepreneurship is a disease that never sets you free. But if you have the guts to focus on your own, you're not. signal, own your own setbacks completely, and take care of your mind and body, then you have
Starting point is 01:14:38 what it takes to make it through the valley of death and come out the other side, victorious. Thank you for listening to this episode of Young and Profiting Podcast. If you listen learned and profited from this conversation with the incredible Kevin O'Leary, then share it with somebody who needs to hear these hard truths about entrepreneurship. And if you enjoyed this episode and learned something valuable, I'd really appreciate it if you left us a five-star written review on Apple Podcast, Spotify, or CastBox. Your support helps more people discover young and profiting and allows us to bring a powerhouse guest like Kevin O'Leary on more often.
Starting point is 01:15:10 You can also find me on Instagram at Yap with Hala or LinkedIn by searching my name. It's Hala Taha. And before we wrap up, I want to give an incredible shout out to my guest outreach team for always being on top of their game. Shout out to Hasham, Fricon, and Joshua for absolutely crushing it and for snagging an incredible guests like Kevin or Lirie. Until next time, this is your host, Halataha, aka the podcast Princess. signing off.

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